First boat?

[cemdev]

Hi,

I'm contemplating buying my first boat, and am considering the aventura 37 and nautitech open 40.

I sailed dinghies extensively as a kid, owned a laser and Hobie 16 and a couple of others. Have crewed a couple of times on larger monos for a week or two at a time, but have very limited experience on anything over 20 foot.

My heart is set on a cat. That said, there is part of me thinking it would be wiser to buy a cheaper used mono for a season first to get some experience.

Money's not really tight, but it sounds like I would have a hard time getting insurance on a new cat and I would definitely want that.

So, my question are.

1. Does it make sense to buy a sub $100K mono for 6-8 months to get experience?
2. Would that be enough experience to assist with getting insurance when I got a cat?
3. Are there any other 35-40ft cats I should be looking at? I want something that feels like sailing, not like a tank, has reasonable performance, that has decent salon/cockpit space and room for kitesurfing gear. Would be just 2 people. Not as concerned about berths, so narrow hulls would likely be a better option.
4. Are there any great places/times of year to find a good deal on mono I would only have a short while?

Currently in latam, so would buy anywhere between Southern USA and Panama.

Whatever I get, I'd hire an experienced skipper for the first week or two to get me up and running.